Watertown, CT Horseback Riding Trails and Maps

1357 Reviews

Looking for the best Horseback Riding trails around Watertown?

Find the top rated horseback riding trails in Watertown, whether you're looking for an easy short horseback riding trail or a long horseback riding trail, you'll find what you're looking for. Click on a horseback riding trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
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6 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

60.3 mi
State: CT
Ballast, Crushed Stone, Dirt, Gravel

Hop River State Park Trail

20 mi
State: CT
Crushed Stone

Larkin State Park Trail

10.8 mi
State: CT
Cinder, Crushed Stone, Dirt, Gravel

New Milford River Trail

5 mi
State: CT
Asphalt, Crushed Stone, Dirt

Old Croton Aqueduct Trail

26.5 mi
State: NY
Crushed Stone, Dirt, Grass, Gravel

Railroad Ramble

1.7 mi
State: CT
Asphalt, Dirt, Grass
Trail Image Trail Name States Length Surface Rating
Overview The Air Line State Park Trail winds 60.3 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway...
CT 60.3 mi Ballast, Crushed Stone, Dirt, Gravel
It’s hard to pick a favorite season to experience the Hop River State Park Trail, set amid the dense forests of Eastern Connecticut. Sections of the 20-mile rail-trail dive through steep rock cuts...
CT 20 mi Crushed Stone
The Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. The rail-trail follows the route of the New York & New England...
CT 10.8 mi Cinder, Crushed Stone, Dirt, Gravel
The first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....
CT 5 mi Asphalt, Crushed Stone, Dirt
Overview The Old Croton Aqueduct Trail spans 26.5 miles across West Chester County, NY. It is often a singletrack dirt pathway that winds through communities and trees and provides an oasis of...
NY 26.5 mi Crushed Stone, Dirt, Grass, Gravel
The Railroad Ramble occupies a corridor abandoned by the Central New England Railroad, which provided service from 1871 through 1967. In Lakeville, the trail can be found just off of Route 41 behind...
CT 1.7 mi Asphalt, Dirt, Grass

Recent Trail Reviews

Pequonnock River Trail

Bring your phone with GPS

May, 2024 by sboaters_tl

My wife and I did this trail on touring bikes, starting at Glenwood Park in Bridgeport, and proceeded northward. Easy to follow until Twin Brooks Park where the trail joins the park trails but there is no signage from here northward. Nice surface but we had to stop NUMEROUS times to look at our GPS to determine our location and which trail/path to take. Then finding the Tait Road starting point for the next section was a challenge. Either print out the Trail Description and have a map, and/or have your phone handy as there are very few, if any, signs showing where the trail goes. A nice series of trails once you find them but don't expect ANY directional advice.

North Shore Rail Trail

Relaxed ride for family

May, 2024 by qfranco10

Yes it's along powerlines, but the ride is nice and easy, there are a few places to stop and enjoy a break. Most road crossings have crossing lights.

CTfastrak Multi-Use Trail

Trail starts downtown New Britian, easy to find. Trail was clean, well marked except when you hit the main road for a little distance. Not a lot of people on 5/25/24. There's not a lot to look at but a nice 4.4 Mile trail.

May, 2024 by carlosccalhoun

Trail starts downtown New Britian, easy to find. Trail was clean, well marked except when you hit the main road for a little distance. Not a lot of people on 5/25/24. There's not a lot to look at but a nice 4.4 Mile trail.

Accordion

Old Croton Aqueduct Trail

great view the whole time

May, 2024 by smashwin111

This and the Erie Path on the other side of the river are relatively flat, and I rode both easily on a hybrid. The view on either side of the river is really nice the whole time, because your are just elevated enough to see the river clearly the whole time. Also Tarrytown is a nice stop. I did this in two legs - Yonkers to Tarrytown, and Tarrytown to Croton Reservoir. The reservoir at the end is a nice destination.

Harlem Valley Rail Trail

Harlem River Trail

May, 2024 by johnecarl

This is a great trail. Great scenery and well paved. The northern part is partially under repair and new pavement so you have may to go to a starting point a little further south

Farmington Canal Heritage Trail

Farmington/Heritage

May, 2024 by blujeepin76

Over run with cyclists. Many very inconsiderate. They don’t ring their bell until right behind you. Should be a biking speed limit. Many older people can’t move out of the way when there are pairs of cyclists that stay side by side. Extremely inconsiderate. Not all but too many are.

North Shore Rail Trail

Fairly flat

May, 2024 by z4g9gshqpr

Only two things keeping this from being a 5 star are the numerous road crossings and the fact that the trail is under power lines. Best in the area.

Bronx River Greenway

Almost perfect for cyclist

May, 2024 by toddwrobinson_tl

We started in Bronxville and the beginning of the trail was a bit "annoying" with a bunch of people walking. We weren't sure if we would enjoy this trail...boy did that change. The trail to Kensico Dam was full of surprises, the good kind. A bunch of twist and turns with some fun hills. We'll be going back! We grabbed some sandwiches in Bronxville (Lange's Delicatessen) after our ride before heading home. A perfect day, 24 miles roundtrip.

Pequonnock River Trail

outstanding!

May, 2024 by iemontejo

Make sure to understand the trail entry points!

Harlem Valley Rail Trail

Perfection in imperfection

May, 2024 by john9mcnulty

Several sections of the trail are currently closed between Copake and Millerton. Although I wouldn't recommend them to everyone, I considered them very rideable or walkable. I'd probably start a few stops down next time, but only to avoid rerouting if they were actually doing maintenance and wouldn't let me pass though. When I wasn't considering alternative routes I was overtaken by the scenery between Copake and Milerton. The wildlife and landscapes were seldom disappointing, but the countless bugs were distracting. Milerton to Wassaic was underwhelming if you've drove along 22 before. Strangely, it was in worse condition than the closed sections. Scattered frost heaves sent cyclist darting around the trail or shot out of their saddle and skateboards trying to break their fall. Knowing this made it easier on the way back, but also way slower.

Cannot say this enough. I rode into more bugs in 4h on this trail than I have in over 4000 miles anywhere else.

TLDR:
This trail is currently "closed" for several miles. The trail is full of stunning scenery, bumps, and bugs. Well worth visiting, but keep expectations in check. Would give 3.75 if it was an option.

Litchfield Community Greenway

Great Trail!

April, 2024 by edupont88

Great trail through White Memorial Wildlife Preserve. Bantam section not complete yet, but still worth an out-and-back ride. Lunch in Litchfield, ice cream in Bantam.

Hudson Valley Rail Trail

A change in scenery

April, 2024 by robert.richter89

I rode both the William Stienhaus trail and the Hudson Valley Trail on a very windy early April Sunday. In comparison to the Stienhaus trail the Hudson Valley Trail is not as well marked but is also wide and in great condition like the Stienhaus trail. The Hudson Trail is overall more consistently scenic with less residential and commercial areas until you get to the end which runs right next to RT 9.

There are a few options to take a path of the trail to go into Highland which offers a few places to eat. My only complaint is that there is that there is no clear signage that the Hudson Valley Trail ended so I rode about a mile adjacent to RT 9 before realizing that the Hudson Valley trail technically ended at a small parking lot.

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